A shell script to build openssl for iOS and Mac. It currently builds: Mac -> i386 & x86_64 // iOS -> armv7, arm64 // iOS Simulator -> i386 & x86_64.

openssl-build.sh

#!/bin/bash

# This script builds the iOS and Mac openSSL libraries
# Download openssl http://www.openssl.org/source/ and place the tarball next to this script

# Credits:
# https://github.com/st3fan/ios-openssl
# https://github.com/x2on/OpenSSL-for-iPhone/blob/master/build-libssl.sh


set -e

usage ()
{
	echo "usage: $0 [minimum iOS SDK version (default 8.2)]"
	exit 127
}

if [ $1 -e "-h" ]; then
	usage
fi

if [ -z $1 ]; then
	SDK_VERSION="8.2"
else
	SDK_VERSION=$1
fi

OPENSSL_VERSION="openssl-1.0.1m"
DEVELOPER=`xcode-select -print-path`

buildMac()
{
	ARCH=$1

	echo "Building ${OPENSSL_VERSION} for ${ARCH}"

	TARGET="darwin-i386-cc"

	if [[ $ARCH == "x86_64" ]]; then
		TARGET="darwin64-x86_64-cc"
	fi

	pushd . > /dev/null
	cd "${OPENSSL_VERSION}"
	./Configure ${TARGET} --openssldir="/tmp/${OPENSSL_VERSION}-${ARCH}" &> "/tmp/${OPENSSL_VERSION}-${ARCH}.log"
	make >> "/tmp/${OPENSSL_VERSION}-${ARCH}.log" 2>&1
	make install >> "/tmp/${OPENSSL_VERSION}-${ARCH}.log" 2>&1
	make clean >> "/tmp/${OPENSSL_VERSION}-${ARCH}.log" 2>&1
	popd > /dev/null
}

buildIOS()
{
	ARCH=$1

	pushd . > /dev/null
	cd "${OPENSSL_VERSION}"
  
	if [[ "${ARCH}" == "i386" || "${ARCH}" == "x86_64" ]]; then
		PLATFORM="iPhoneSimulator"
	else
		PLATFORM="iPhoneOS"
		sed -ie "s!static volatile sig_atomic_t intr_signal;!static volatile intr_signal;!" "crypto/ui/ui_openssl.c"
	fi
  
	export $PLATFORM
	export CROSS_TOP="${DEVELOPER}/Platforms/${PLATFORM}.platform/Developer"
	export CROSS_SDK="${PLATFORM}${SDK_VERSION}.sdk"
	export BUILD_TOOLS="${DEVELOPER}"
	export CC="${BUILD_TOOLS}/usr/bin/gcc -arch ${ARCH}"
   
	echo "Building ${OPENSSL_VERSION} for ${PLATFORM} ${SDK_VERSION} ${ARCH}"

	if [[ "${ARCH}" == "x86_64" ]]; then
		./Configure darwin64-x86_64-cc --openssldir="/tmp/${OPENSSL_VERSION}-iOS-${ARCH}" &> "/tmp/${OPENSSL_VERSION}-iOS-${ARCH}.log"
	else
		./Configure iphoneos-cross --openssldir="/tmp/${OPENSSL_VERSION}-iOS-${ARCH}" &> "/tmp/${OPENSSL_VERSION}-iOS-${ARCH}.log"
	fi
	# add -isysroot to CC=
	sed -ie "s!^CFLAG=!CFLAG=-isysroot ${CROSS_TOP}/SDKs/${CROSS_SDK} -miphoneos-version-min=${SDK_VERSION} !" "Makefile"

	make >> "/tmp/${OPENSSL_VERSION}-iOS-${ARCH}.log" 2>&1
	make install >> "/tmp/${OPENSSL_VERSION}-iOS-${ARCH}.log" 2>&1
	make clean >> "/tmp/${OPENSSL_VERSION}-iOS-${ARCH}.log" 2>&1
	popd > /dev/null
}

echo "Cleaning up"
rm -rf include/openssl/* lib/*

mkdir -p lib/iOS
mkdir -p lib/Mac
mkdir -p include/openssl/

rm -rf "/tmp/${OPENSSL_VERSION}-*"
rm -rf "/tmp/${OPENSSL_VERSION}-*.log"

rm -rf "${OPENSSL_VERSION}"

if [ ! -e ${OPENSSL_VERSION}.tar.gz ]; then
	echo "Downloading ${OPENSSL_VERSION}.tar.gz"
	curl -O https://www.openssl.org/source/${OPENSSL_VERSION}.tar.gz
else
	echo "Using ${OPENSSL_VERSION}.tar.gz"
fi

echo "Unpacking openssl"
tar xfz "${OPENSSL_VERSION}.tar.gz"

buildMac "i386"
buildMac "x86_64"

echo "Copying headers"
cp /tmp/${OPENSSL_VERSION}-i386/include/openssl/* include/openssl/

echo "Building Mac libraries"
lipo \
	"/tmp/${OPENSSL_VERSION}-i386/lib/libcrypto.a" \
	"/tmp/${OPENSSL_VERSION}-x86_64/lib/libcrypto.a" \
	-create -output lib/Mac/libcrypto.a

lipo \
	"/tmp/${OPENSSL_VERSION}-i386/lib/libssl.a" \
	"/tmp/${OPENSSL_VERSION}-x86_64/lib/libssl.a" \
	-create -output lib/Mac/libssl.a

buildIOS "armv7"
buildIOS "arm64"
buildIOS "x86_64"
buildIOS "i386"

echo "Building iOS libraries"
lipo \
	"/tmp/${OPENSSL_VERSION}-iOS-armv7/lib/libcrypto.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-arm64/lib/libcrypto.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-i386/lib/libcrypto.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-x86_64/lib/libcrypto.a" \
	-create -output lib/iOS/libcrypto.a

lipo \
	"/tmp/${OPENSSL_VERSION}-iOS-armv7/lib/libssl.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-arm64/lib/libssl.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-i386/lib/libssl.a" \
	"/tmp/${OPENSSL_VERSION}-iOS-x86_64/lib/libssl.a" \
	-create -output lib/iOS/libssl.a

echo "Cleaning up"
rm -rf /tmp/${OPENSSL_VERSION}-*
rm -rf ${OPENSSL_VERSION}

echo "Done"

For anyone interested. You can try this repo https://github.com/sinofool/build-openssl-ios I've had success with this.